Optically active isosorbide derivative and optically active isomannide derivative, production methods thereof, photo-reactive chiral agent, liquid crystal composition, liquid crystal color filter, optical film and recording medium, method for changing helical structure of liquid crystal and method for fixing helical structure of liquid crystal

Abstract

The invention relates to an optically active isosorbide derivative represented by general formula (I) and an optically active isomannide derivative represented by general formula (V), wherein R 1 and R 9 each independently represent an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group or —NR 17 R 18 , wherein R 17 and R 18 each independently represent a hydrogen atom, an alkyl group or an aryl group; R 2 and R 10 each independently represent a hydrogen atom, an alkyl group or an aryl group; R 3 to R 6 and R 11 to R 14 each independently represent a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group; R 7 , R 15 , R 8 and R 16 each independently represent a hydrogen atom or an alkyl group; and R 2 and R 4 , and R 10 and R 12 may in each combination be combined with each other to form a 5- or 6-membered ring.

1. An optically active isosorbide derivative represented by the following general formula (I): 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       2. A method of producing an optically active isosorbide derivative represented by the following general formula (I), wherein aryl halides represented by the following general formulae (II) and (III) and an isosorbide derivative represented by the following general formula (IV) are made to react with each other: 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group;  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring;  
 R 31  to R 46  each respectively and independently represent members that are equivalent to those represented by R 1  to R 16  in the general formula (I); and  
 X 21  and X 22  each independently represent a halogen atom.  
 
     
     
       3. A photo-reactive chiral agent comprising an optically active isosorbide derivative represented by the following general formula (I) 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 8 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       4. A liquid crystal composition comprising at least one liquid crystalline compound and at least one type of an optically active isosorbide derivative represented by the following general formula (I) 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       5. The liquid crystal composition according to  claim 4 , further comprising a photo-polymerization initiator, wherein the liquid crystalline compound has at least one polymerizable group. 
     
     
       6. The liquid crystal composition according to  claim 5 , wherein the optically active isosorbide derivative and the photo-polymerization initiator each have a different photosensitive wavelength region from each other. 
     
     
       7. A method for changing a helical structure of liquid crystal, wherein a structure of an optically active isosorbide derivative represented by the following general formula (I) is changed by irradiating light to a liquid crystal composition comprising at least one liquid crystalline compound and at least one type of the optically active isosorbide derivative represented by the following general formula (I) 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       8. A method for fixing a helical structure of liquid crystal, the method comprising the steps of:
 imagewise irradiating light having a wavelength within a photosensitive wavelength region of an optically active isosorbide derivative represented by the following general formula (I) to a liquid crystal comprising at least one liquid crystalline compound having at least one polymerizable group, at least one type of the optically active isosorbide derivative represented by the general formula (I), and a photo-polymerization initiator; and  
 irradiating light having a wavelength region within a photosensitive wavelength region of the photo-polymerization initiator agent to the thus-irradiated liquid crystal composition to perform photo-polymerization 
                 
 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       9. A liquid crystal color filter comprising at least one liquid crystalline compound and at least one type of an optically active isosorbide derivative represented by the following general formula (I) 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       10. An optical film comprising at least one liquid crystalline compound and at least one type of an optically active isosorbide derivative represented by the following general formula (I) 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       11. A recording medium comprising at least one liquid crystalline compound and at least one type of an optically active isosorbide derivative represented by the following general formula (I) 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       12. An optically active isomannide derivative represented by the following general formula (V): 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17  R 8 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       13. A method of producing an optically active isomannide derivative represented by the following general formula (V), wherein aryl halides represented by the following general formulae (II) and (III) and an isomannide derivative represented by the following general formula (VI) are made to react with each other: 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group;  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring;  
 R 31  to R 46  respectively and independently represent members that are equivalent to those represented by R 1  to R 16  in the general formula (V); and  
 X 21  and X 22  each independently represent a halogen atom.  
 
     
     
       14. A photo-reactive chiral agent comprising an optically active isomannide derivative represented by the following general formula (V) 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       15. A liquid crystal composition comprising at least one liquid crystalline compound and at least one type of an optically active isomannide derivative represented by the following general formula (V) 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       16. The liquid crystal composition according to  claim 15  comprising a photo-polymerization initiator, wherein the liquid crystalline compound has at least one polymerizable group. 
     
     
       17. The liquid crystal composition according to  claim 16 , wherein the optically active isomannide derivative and the photo-polymerization initiator each have a different photosensitive wavelength region from each other. 
     
     
       18. A method for changing a helical structure of liquid crystal, wherein a structure of an optically active isomannide derivative represented by the following general formula (V) is changed by irradiating light to a liquid crystal composition comprising at least one liquid crystalline compound and at least one type of an optically active isosorbide derivative represented by the following general formula (V) 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       19. A method for fixing a helical structure of liquid crystal, the method comprising the steps of:
 imagewise irradiating light having a wavelength within a photosensitive wavelength region of an optically active isomannide derivative represented by the following general formula (V) to a liquid crystal composition comprising at least one liquid crystalline compound having at least one polymerizable group, at least one type of the optically active isosorbide derivative represented by the general formula (V) and a photo-polymerization initiator; and  
 irradiating light having a wavelength within a photosensitive wavelength region of the photo-polymerization initiator agent to the thus-irradiated liquid crystal composition to perform photo-polymerization 
                 
 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       20. A liquid crystal color filter comprising at least one liquid crystalline compound and at least one type of an optically active isomannide derivative represented by the following general formula (V) 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       21. An optical film comprising at least one liquid crystalline compound and at least one type of an optically active isomannide derivative represented by the following general formula (V) 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.  
 
     
     
       22. A recording medium comprising at least one liquid crystalline compound and at least one type of an optically active isomannide derivative represented by the following general formula (V) 
                 
 wherein R 1  and R 9  each independently represent a member selected from the group consisting of an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group and —NR 17 R 18 , wherein R 17  and R 18  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 2  and R 10  each independently represent a member selected from the group consisting of a hydrogen atom, an alkyl group and an aryl group;  
 R 3  to R 6  and R 11  to R 14  each independently represent a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group and an alkoxy group;  
 R 7 , R 15 , R 8  and R 16  each independently represent a hydrogen atom or an alkyl group; and  
 R 2  and R 4 , and R 10  and R 12  may in each combination be combined with each other to form a 5- or 6-membered ring.